Lithium cobalt-bis-dicarbollide catalyzed substitution reactions of allylic acetates

Tetrahedron Letters

Volumn 37, Issue 48, 1996, Pages 8707-8710

  Grieco, Paul A ^a   DuBay, William J ^a   Todd, Lee J ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; FUNCTIONAL GROUP; LITHIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE;

EID: 0030602224     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02021-7     Document Type: Article

References (10)

1. 1. Grieco, P.A.; Collins, J.L.; Henry, K.J., Jr. Tetrahedron Lett. 1992, 33, 4735. Henry, K.J., Jr.; Grieco, P.A. J. Chem. Soc., Chem. Commun. 1993, 510. Pearson, W.H.; Schkeryantz, J.M. J. Org. Chem. 1992, 57, 2986.
2. 1. Grieco, P.A.; Collins, J.L.; Henry, K.J., Jr. Tetrahedron Lett. 1992, 33, 4735. Henry, K.J., Jr.; Grieco, P.A. J. Chem. Soc., Chem. Commun. 1993, 510. Pearson, W.H.; Schkeryantz, J.M. J. Org. Chem. 1992, 57, 2986.
3. 1. Grieco, P.A.; Collins, J.L.; Henry, K.J., Jr. Tetrahedron Lett. 1992, 33, 4735. Henry, K.J., Jr.; Grieco, P.A. J. Chem. Soc., Chem. Commun. 1993, 510. Pearson, W.H.; Schkeryantz, J.M. J. Org. Chem. 1992, 57, 2986.
4. 2. DuBay, W.J.; Grieco, P.A.; Todd, L.J. J. Org. Chem. 1994, 59, 6898.
5. 2 (9.1 mg, 0.028 mmol) under argon was added 109 μL of 1-methoxy-1-(tert-butyldimethylsilyl)oxy)ethylene (104 mg, 0.55 mmol). The reaction was stirred at ambient temperature. After 24 h, the reaction was quenched with a saturated sodium bicarbonate solution. The product was isolated by extraction with ether. The combined organic extracts were dried over anhydrous magnesium sulfate and concentrated in vacuo. Flash chromatography employing 5% ether/hexane gave rise to 48 mg (81%) of 3.
6. 4. Casnati, G.; Francioni, M.; Guareschi, A.; Pochini, A. Tetrahedron Lett. 1969, 10, 2485. Casnati, G.; Dossena, A.; Pochini, A. Tetrahedron Lett. 1972, 13, 5277. Ganesan, A.; Heathcock, C.H. Tetrahedron Lett. 1993, 34, 439.
7. 4. Casnati, G.; Francioni, M.; Guareschi, A.; Pochini, A. Tetrahedron Lett. 1969, 10, 2485. Casnati, G.; Dossena, A.; Pochini, A. Tetrahedron Lett. 1972, 13, 5277. Ganesan, A.; Heathcock, C.H. Tetrahedron Lett. 1993, 34, 439.
8. 4. Casnati, G.; Francioni, M.; Guareschi, A.; Pochini, A. Tetrahedron Lett. 1969, 10, 2485. Casnati, G.; Dossena, A.; Pochini, A. Tetrahedron Lett. 1972, 13, 5277. Ganesan, A.; Heathcock, C.H. Tetrahedron Lett. 1993, 34, 439.
9. 5. The chemistry of weakly coordinating anions has been the subject of much interest recently (Strauss, S. H. Chem. Rev. 1993, 93, 927).
10. 6. For a review of transition metal chemistry, see: Godleski, S.A. in Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Vol 4, pp 585-661.